Crystalline form of 1′-(1-methylethyl)-4′-[(2-fluoro-4-methoxyphenyl)methyl]-5′-methyl-1H-pyrazol-3′-O-β-D-glucopyranoside, a method for its preparation and the use thereof for preparing medicaments

Abstract

The invention relates to a crystalline form of 1′-(1-methylethyl)-4′-[(2-fluoro-4-methoxyphenyl)methyl]-5′-methyl-1H-pyrazol-3′-O-β-D-glucopyranoside, to a method for the preparation thereof, as well as to the use thereof for preparing medicaments.

1. Crystalline form of 1′-(1-methylethyl)-4′-[(2-fluoro-4-methoxyphenyl)methyl]-5′-methyl-1H-pyrazol-3′-O-β-D-glucopyranoside having an X-ray powder diffraction pattern that comprises peaks at 5.35, 10.76 and 16.20 degrees 2Θ (±0.1 degrees 2Θ), wherein said X-ray powder diffraction pattern is made using CuK α1  radiation. 
     
     
       2. Crystalline form according to  claim 1  wherein the X-ray powder diffraction pattern further comprises peaks at 9.31 and 19.81 degrees 2Θ (±0.1 degrees 2Θ), wherein said X-ray powder diffraction pattern is made using CuK α1  radiation. 
     
     
       3. Crystalline form according to  claim 1 , wherein the X-ray powder diffraction pattern further comprises peaks at 14.27, 18.25 and 23.27 degrees 2Θ (±0.1 degrees 2Θ), wherein said X-ray powder diffraction pattern is made using CuK α1  radiation. 
     
     
       4. Crystalline form according to  claim 1 , characterized in that it comprises water in the range from 0 to 10 weight-%. 
     
     
       5. 1′-(1-methylethyl)-4′-[(2-fluoro-4-methoxyphenyl)methyl]-5′-methyl-1H-pyrazol-3′-O-β-D-glucopyranoside wherein at least 50% by weight of said substance is present in the form of a crystalline form in accordance with  claim 1 . 
     
     
       6. A pharmaceutical composition comprising a crystalline form according to  claim 1 . 
     
     
       7. A method for making a crystalline form in accordance with  claim 1  said method comprising the following steps:
 (a) dissolving the compound of the formula I 
 
       
         
           
           
               
               
           
         
       
       in a solvent or a mixture of solvents to form a solution;
 (b) storing the solution to precipitate the crystalline form out of solution and thus to yield a suspension; 
 (c) isolating the precipitate from the suspension; and 
 (d) drying the precipitate optionally until an excess of said solvent or mixture of solvents has been removed. 
 
     
     
       8. The method according to  claim 7 , wherein in step (a) and/or step (b) one or more antisolvents are added. 
     
     
       9. The method according to  claim 7 , wherein the staining material of the compound of the formula I and/or said solvent or mixture of solvents contain at least an amount of 0.5 mol H 2 O per mol of the compound of the formula I. 
     
     
       10. Crystalline form according to  claim 4 , characterized by a content of water in the range from about 0.5 to 4.0 weight-% at a relative humidity between 30 and 50%.